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Mila: OTK Just Because 1 Mila: OTK Just Because 2 Mila: OTK Just Because 3 Mila: OTK Just Because 4
Mila: OTK Just Because
Mila is given a OTK spanking by the Headmaster just because he wants to. He starts with hand and moves on to hairbrush and hugs.
Updated: Fri. May. 02, 2025
Brooke: Bedroom Punishment 1 Brooke: Bedroom Punishment 2 Brooke: Bedroom Punishment 3 Brooke: Bedroom Punishment 4
Brooke: Bedroom Punishment
The Headmaster punishes Brooke in her bedroom with hand, hairbrush and a painful wooden scrub brush, first over her panties, then on-the-bare and finally completely naked.
Updated: Wed. Apr. 30, 2025
Daija: Going Out While Grounded 1 Daija: Going Out While Grounded 2 Daija: Going Out While Grounded 3 Daija: Going Out While Grounded 4
Daija: Going Out While Grounded
The Headmaster learns that Daija has been sneaking out while she has been grounded and confined to the house. He takes her OTK and uses a hairbrush on her shapely bottom. Her squirming and crying suggests that he made his point.
Updated: Mon. Apr. 28, 2025
Mila: Cooking a Little Breakfast 1 Mila: Cooking a Little Breakfast 2 Mila: Cooking a Little Breakfast 3 Mila: Cooking a Little Breakfast 4
Mila: Cooking a Little Breakfast
Poor lovely simple minded Mila struggles to prepare even a simple breakfast for Headmaster Ken. He orders her naked as he punishes her with a yardstick across her shapely bottom.
Updated: Fri. Apr. 25, 2025
Daija: Paddled Hard 1 Daija: Paddled Hard 2 Daija: Paddled Hard 3 Daija: Paddled Hard 4
Daija: Paddled Hard
The Headmaster discovers Daija has been sending nude photos to her boyfriend. Her orders her to strip nude and bend over and grab her ankles for a hard painful paddling.
Updated: Wed. Apr. 23, 2025
Madison: Messy Kitchen 1 Madison: Messy Kitchen 2 Madison: Messy Kitchen 3 Madison: Messy Kitchen 4
Madison: Messy Kitchen
Waify yet incompetent Madison finds it impossible to keep the kitchen clean. The Headmaster helps motivate her with face slaps and an OTK hand spanking.
Updated: Mon. Apr. 21, 2025
Tabitha: Naked OTK 1 Tabitha: Naked OTK 2 Tabitha: Naked OTK 3 Tabitha: Naked OTK 4
Tabitha: Naked OTK
Naked, lovely and tattooed Tabitha goes over the Headmaster's loving knee for a lengthy OTK hand-spanking. Afterward she is posed and photographed.
Updated: Fri. Apr. 18, 2025
Daija: OTK - Hairbrush and Paddle 1 Daija: OTK - Hairbrush and Paddle 2 Daija: OTK - Hairbrush and Paddle 3 Daija: OTK - Hairbrush and Paddle 4
Daija: OTK - Hairbrush and Paddle
The Headmaster gently counsels Daija on the importance of keeping her personal space neat and tidy. She goes over his knee for a painful dose of the hairbrush and paddle.
Updated: Wed. Apr. 16, 2025
Zara: Submissive Training 1 Zara: Submissive Training 2 Zara: Submissive Training 3 Zara: Submissive Training 4
Zara: Submissive Training
Zara continues along her path to submissiveness, helped, as always, by the Headmaster's gentle guidance. Already stripped naked, and with a very bruised and sore bottom, she goes over the Headmaster's knee for a long slow hand spanking.
Updated: Mon. Apr. 14, 2025
Jenna: Return to the Punishment Room 1 Jenna: Return to the Punishment Room 2 Jenna: Return to the Punishment Room 3 Jenna: Return to the Punishment Room 4
Jenna: Return to the Punishment Room
Naked Jenna is bound with her hands above her head and punished by the Headmaster with crop and strap.
Updated: Fri. Apr. 11, 2025
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